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I always look forward to date nights and there is always one indicator of a fun, enjoyable evening: feeling comfortable! Nothing ruins the evening faster than feeling uncomfortable in your outfit (or shoes). I always try to find clothing items that can survive dinner and pumps that can handle more than ten minutes. Although it obviously depends on the activity, this dress and heels can be dressed up or down with only a few exchanges. Cross-body bags are always useful on dates–so very convenient!